Learning to dress your body in a way that expresses your creativity and tastes

Accessing that third level through expressive dressing can help foster self-love and self-respect while simultaneously providing a fun and rewarding creative outlet. But tackling the first two is what makes that third one truly possible. Many of us try to skip to expressing our creativity through personal style, but in my experience, doing so before making serious strides toward self love AND sussing out how you want your style and body to interact often leads to frustration, confusion, and backtracking.

Learning about your body first makes jumping to levels two and three easier and more rewarding.

You make some great points. I think I am in a constant flux between the 3. Everyone has “fat” days where they feel like nothing fits; it’s being able to accept those that takes time! I think I am most working on step 3 – finding a creative style that I think expresses who I am.

Jenna

Although I’ve struggled some with all three levels (as I imagine all women have, to some degree), the third one definitely resonates with me right now. I’ve been trying to come to terms with the gap between my personal taste and what the world of fashion says I should like and wear. I like trends, and I enjoy incorporating something new and exciting into my wardrobe, but there are some trends that seem so ubiquitous that I feel almost embarrassed for not wearing them.

Take scarves, for example. I just plain don’t like the way scarves look on me, though I may appreciate how they look on others. I think it has something to do with proportions and where I like to place volume on my body, plus I’ve never been a huge accessorizer (I prefer simple accessories and maybe one bold item of clothing). And yet, I feel like I’m an amateur or something for not wearing scarves well, so I’ve purchased some that I never wear.

Anonymous

I know what you mean. I did the same exact thing! I bought three scarves, and I never wear them!

I do love your posts. For me, number 1 is coming about as a result of the progress I’m making in 2 & 3. But then I’ve always suspected I’m a bit upside down and back to front (in a good self loving way of course!)!!
Px

Roxxi

Hi, Sal. Great post, thanks 🙂
I agree that it’s usually more effective to focus on loving your body before trying to develop your own style, since you’ll be more attuned to how your body likes to look. But sometimes, depending on what the actual body image struggle is, forcing ourselves to dress in a way that celebrates our bodies (I’m speaking based on my own experience) kind of makes us realise that we look just fine, after all. And then that can in turn cause us to love our bodies more. I don’t remember if I started appreciating my body before I started taking time to dress myself in a way that was more flattering to my shape (small and thin, with an hourglass shape) or if they happened at the same time. It was before I stumbled upon your blog, so I just sort of tried different things until I found one that worked.
And in answer to your question, I’m at step 3 🙂 I’ve realised I really like pencil skirts and ruffle-y tops, and splashes of bright colour. Now, I *like* getting dressed up, and I get a lot of compliments on my style, because I’ve figured out how to make my clothes look exactly like me 🙂
The reason I like yours better is that it tackles the root of the problem first. Because if you love your body, and have found that you really like clothes that are outside what people would usually gravitate towards, you’ll be more confident should they choose to act all snarky about it.
And even though it took me about three years (I’m 19 now), the result is so rewarding that I’d go through the whole thing again, just to experience it. I never realised that the way I feel about my body is linked to so many things! I feel happier, more comfortable sharing my opinion whether or not people will agree with me, and most importantly, I feel better about standing up for myself.

I go up-and-down. When I was a size 4, it was a struggle to stay there. My mom is ~92 pounds and her side of the family is tiny. I take after my dad’s side which if I base things on my aunt, the women are more curvy. I like my curves. I don’t want to say that I gave up or got comfortable, but I’m happily married to a chef and I love food. I don’t have a high metabolism.

I wouldn’t mind losing weight, but I’m happy where I am. My husband still finds me attractive after 14 years (he told menthat recently). I have to admit that when I visit pette forums, I feel like Goliath. I fit the definition fashion-wise because I’m only 4’11”, but not as I think the general public defines “Petite.” I’m not a size 00P like so many other petite bloggers. Yay for them, yay for my (pushing the limits of) size 8. I think I often dress in a way that people can’t tell I weigh (ahem) pounds.

For the most part, I totally agree. I think these are each crucial steps to being stylish. The one question I have, and I definitely don’t have an answer for this, is whether or not the steps have to go in this order. I fully believe that step #1 has to go first, but I think I’m of the opinion that #s 2 and 3 could go in either order, or simultaneously, and eventually end up in the same place. Sometimes, after learning to love and accept your body, it can be important to jump right into expressing your creative self, and then slowly refine that as you figure out what works for you. Thoughts?

Definitely! And as many have pointed out, jumping around among these steps is common, boundary-pushing, and often rewarding.

Charlotte

I agree! Not for a question of one step being more valuable than another, but because of my own experience: I’ve skipped step 2! I don’t “see” my body, except for colouring. I care very much about how it feels, but I just can’t seem to wrap my head around “figure-flattery”. The only proportions I seem to perceive are those of the clothes.
I’m trying, but I very sincerely have no idea what my figure assets and weaknesses are!

I have a few self-esteem issues and I constantly diet because I’m never “thin” enough, but these don’t affect the way I dress – at least, not on a conscious level. I think the first statement holds more true for me – having fun with what I wear makes me appreciate my body and love myself more than just plain old trying to love my body as it is because I *should*. To be perfectly honest, I take outfit photos not only to document my evolving style, but also because that’s the only time I get to appreciate how pretty I am. I don’t always feel that way when I look at myself in the mirror.

My body and I are pretty much at peace, and I think I know what flatters my figure and I’m done trying to fit into style boxes (like the high tight waist belt and 50s silhouette) that I’m not comfortable in. But in terms of creative expression, I’m just getting started.

Jennifer M

I do agree but would like to add a step that factors in your job and your lifestyle. My sartorial evolution has always been spurred by life events like college, job changes, and becoming a parent, along with accepting the ever-changing shape of your body. While number “1. Learning to love and accept your body as it is” is something that we can start learning and teaching at a young age, because your body and circumstances change so often we are often starting all over again, back at step 1. But doesn’t that make things exciting? Then your old outfits or favorite pieces are associated with your former self, so that army jacket will always remind you of high school, or that bag of the summer you spent travelling, and your leopard flats of your last month of pregnancy. It’s fun to speculate too: What will I dress like when I retire? What will I end up wearing to my son’s wedding? Hell, what will I wear on my next vacation? It’s all good fun and it never stops!

Mistie Watkins

I don’t know where I am. I feel like I’m well on my way to being content with my body. I’ve stopped weighing myself and that has really helped. But the other two are hard for me. I’m a stay-at-home and a full-time college student (I also live in Florida), so I tend to gravitate towards jeans and t-shirts or tank tops because they are fast and easy. However, I tend to feel frumpy a lot. Especially when I go out with my friends. When I worked in an office, I loved my wardrobe. It was fun to get dressed in the morning. Now that I have no reason to wear pencil skirts and cardigans, and those things don’t match my needs, I am not as excited about clothing. I’m looking for a way to incorporate the things I liked about business casual into my very, very casual wardrobe, but I’m not sure it is working.

thank you Jennifer M for broadening the territory! Knowing your figure/loving your body/getting in touch with your creativity are all fine and can be part of becoming a stylish person. but there’s so much more!

as Jennifer M points out, there’s your professional life (and your feelings about that, your ambitions and history in your career); your romantic life (what do you want to tell others about availability, orientation, any ‘special interests’); your personal life (family, culture, nationality, any hobbies or compelling interests like dance or travel or painting or). Even more important than relationship to your body, i’ve found, is your relationship to your core self – when you’re right with your soul, love of body comes along easily.

Than there’s the weather.

if any one of these areas (plus some others, i’m sure, and depending on the person) don’t ‘jive’ for the person, then the person won’t feel as stylish as they could.

a seasoned lawyer running around with bed hair and a vintage linen sundress in a chicago snowstorm, on her way to a court hearing, does not come across as stylish. no matter how much that person loves their body and how hot they look in that dress.

As Jennifer M puts it, we’re always changing and that’s what makes all this so fun! It’s also what makes true style such an achievement, and worth striving for. Fascinating discussion!! steph

I feel like I’m pretty good on #1 and #3 but #2 has been the hardest… some things just look so cute on the hanger that I want to buy them even though they are soooo not looking good on my particular figure. Like tent or smock dresses – so cute on the hanger and on girls with a smaller bust, but on me – always look like maternity clothes. I THINK I’ve finally accepted this fact but I still look at them and want them, but now I know enough about my figure to just leave them there.

I started dressing towards my creativity when I was in junior high – before the other two steps were accomplished. I made some of my clothes to suit my tastes, which tended towards “different”. I mean really…I wasn’t wearing Guess jeans and a Benneton top LOL! We definitely couldn’t afford that.

As I have gotten older I have to say that tackling the first two definitely makes the last one much easier. Knowing how any clothes will fit on your body in a flattering way allows you to choose the clothes that will look the best.

I work in a fairly conservative field (financial services), so much of my early career I spent in suits with very little creativity allowed. I am more coming into my own at 37 years of age. I am respected for the work I do, so they tend to overlook some of my more creative outfits. I know the limits of my workplace, though I tend to walk the line at times. Luckily, I it doesn’t affect how I am perceived. At least I don’t think so. 😉

Good list! I recently wrote an article about what personality attributes stylish people typically have, but yes, a healthy relationship with food/weight/your body is probably number one on the list. It’s so true that if you don’t love your body, nothing will look good on you, because the negative feelings you have about your appearance just get in the way. Accepting yourself has nothing to do with your weight, your measurements, or your clothing size – it is always, and only, how you feel about yourself.

I don’t know if I completely agree. I have yet to accept my body for what it is, I’m 44 and I’m always trying to improve my body. Its who I am 😉 But even though I dislike that I wear a size 14 right now, I’m still stylish. Okay, so maybe disliking and trying to improve what I have is accepting? Not sure. I certainly don’t love my body. But I know what looks good on me. I think being a stylish woman is knowing who you are. I have been into fashion since I was 4 years old, I’ve always known what I like, and what I don’t like. So I definitely agree with points 2 and 3 🙂

I love how you broke down those levels. I think self-love is most important. For me, I’ve come a really long way in accepting and loving myself (pudgy stomach and all!) and I think I have a pretty good handle on how to dress myself. The frustrations and the feelings of insecurity about myself comes into play when it times to find those clothes that are suited for me. Being a curvy 16 it can be quite difficult and you can’t help but thinking that you can love yourself all day long but if you can’t find those clothes that will make your body look its best, what’s the point? That’s the time when I feel my self-love waning.

On the one hand, I fully agree with your argument, but on the other, I do think that all three levels are a constant work in progress. I don’t think we ever fundamentally “achieve” the levels and stay there, if that makes sense. After all, life is full of surprises and we go through phases: our bodies change, our personalities, too, to some extent. So I guess I think our target is constantly on the move, and in some sense, we have to try to figure out what those levels of style mean on a daily (or weekly, or monthly, or yearly, or what have you) basis.

I don’t know which stage speaks to me the most right now… There are days when 1 is a given, then there are days when it is far from it. My tastes change dramatically every once in a while, so 3 is definitely a fluid level for me, too. As for 2, I was never good at figuring out what suits my body type, and for whatever reason it doesn’t feel as important to me as the other two.

sally, your blog has always been so inspiring to me – this post is one of the many reasons why! i feel like i’m mostly at number 3, but on some days it’s number 2! like eek said – everyone has “fat” days!

For me, it has been a really complex mingling of all three of those ideas. For example, I experienced a big leap in self love after overcoming some personal health stuff and this, in turn, seemed to increase my ability to feel great in the clothes I wear.

Also, over a long period of time, finding a style that suits me very well on a day to day basis (jeans, boots, great-fitting sweaters (mostly great finds for under 10 bucks at Kohls!), structured coats and simple black dresses).

Finally, I realized recently that I experienced this really profound shift in how I feel about jewelry. Before, I loved to wear costume jewelry. But nowadays I look at all those beaded necklaces, sparkly earrings and cocktail rings with a mix of disdain and disbelief. For some reason, I can’t imagine wearing them anymore. I love my simple, classy pieces (engagement ring, slim watch, pearl necklace, opal earrings). Something about these pieces makes me feel completely amazing.

callie

Despite being voted “Best Dressed” in high school eons ago, it’s taken decades for me to come close to achieving any of the above. My “style” used to be much more based in keeping up with the latest trends, whether or not they were flattering or resonated with who I am. For example, I spent years in a cycle of cutting my hair really short then enduring the unflattering several year process of growing it long again

I suck at hair. I have literally a dozen cowlicks and not particularly attractive hair without spending stupid amounts of time wrangling with it when it is longer. I chopped it into a VERY short pixie about 10 years ago and have never looked back. It’s become my signature “thing”, and lordy, how freeing. 🙂

I literally never have a bad hair day – a quick dousing with water, a towel dry, a little “product” – which can include almost anything on hand in a pinch – and I’m good to go. I cannot tell you how much that has streamlined both my morning routine, and state of mind. It’s also “edgy” enough to circumvent current fashion cycles.

Happily, this has worked well with the evolution of my style – a sleek head works really well with minimalist style, accented by scarves, hats, and statement jewelry.

I’ve been very happy with my body for the past several years (although ageing and watching things fall, down down down is not so fun).

I agree that there are lots of other factors to how you are able to achieve that personal style nirvanna – for me, it was actually blogging plus being in a work environment that permitted me to push boundaries.

Now that I’m out of work, I find that I’m not pushing myself creatively so much on a daily basis – that drive is just not there right now. I do have a much better idea of what clothes and styles really represent my own personal look, but the situation for wearing them has altered substantially. I am excited to get a new job (hopefully soon) and see how my style evolves when I’m in a different environment.

Rachel K

I’ve been trying to figure out how to explain these steps to my 15 yr old step-daughter since she moved in with us last week, but couldn’t quite find the right words. Thank you, Sal, for bulleting them out! My step daughter has a much larger over-all frame than I do, and I can see that it is hard for her that I wear a much smaller size when I’m close to 15 years older than she. I’m taking her shopping this weekend & have been worrying about trying to help her understand that the size on the tag doesn’t matter, its the fit that counts. Her mother has been allowing her to wear clothing that is entirely too small and revealing, her father (my husband) wants me to help her find her own personal style and dress fashionably but appropriately, but 15 is such a fragile age and I’m stressing handling this situation correctly. I think I’m going to show her this post and try to have a conversation with her about the 3 points. I feel like the earlier we learn these things the better off we will be!

Personally, weight lifting has helped me love my small, boyish body. I feel and look more substantial and clothing fits better. 2 is no problem for me, I know what I want to accomplish with my dressing. I’m fully in step 3. I bounce outfits off my husband and even tho it drives him crazy, he gives me honest critiques and I no longer get my feelings hurt if I put together an outfit that doesn’t quite work or is not as I pictured it. Taking photos to assess has helped too, tho I’m not quite ready to post them on the internet. What I’m struggling with right now is not skuwing my outfits too far to the creative/fashion side and away from the professional side. I work at an ad agency, albeit a professional atmosphere, but sometimes I feel like I push the envelope a little far.

I think I found my fashion niche in my early 20’s. I have a strange figure: tiny hips, barrel belly, ample bust, small shoulders, big arms, athletic legs, lollipop head…). Jackie O’s style seemed to flatter me the most, giving me the appearance of hips and minimizing my chest and my waist. I mentioned before that my cats like to use my best clothes as a potty, so I’m stuck here in Portland, looking like a native in jeans, t-shirts, and hoodies (not that it’s bad or anything, and, believe me, it saves a lot of work for this new-ish mother). I’m glad I’m not getting the attention I used to get when I would get all gussied up, but I’m not happy without expressing myself through my sartorial choices. I’m goal for this year is to become the old me…in appearance.